Not every trip can last weeks and take place in a far-off land, at least not as long as you have an employer who expects you to be working more than you’re on vacation. Of course, even if you were an independently wealthy super villain, limiting yourself to big trips would mean missing out on some of the great things a little closer to home. So, time and budget permitting, we try and take shorter weekend trips to get a travel fix while working towards the next big trip.

From Toronto, Boston is only an hour and a half away and proved to be a great destination for a recent weekend trip. Not only is it close enough to make getting in and out in a weekend reasonable, but it’s also pedestrian friendly enough that you can easily see many of the highlights in a short period of time by foot or on public transport. We travelled with a couple of friends, Courtney and Greg, and took advantage of a long weekend to fly down on Friday night and come back on Monday evening.

Go Boston

If you’re planning a trip to Boston, I’d highly recommend checking out the Go Boston card. I’m often a bit leery of tourist promo cards. It always seems like they can offer a lot of small discounts on things that are of no interest to me. While the Go Boston card does have it’s fair share of that, Cape Cod Baseball Hall of Fame and outlet malls come to mind, it does include several discounts that made it worthwhile for us. The price includes a wide range of discounts and freebies. We used the card for the hop-on hop-off trolley, free admission to the aquarium, and a catamaran whale tour.

Starting the trip in style – flying with Porter

Launched in 2006, Porter Airlines has been our favourite airline in North America since then. While it only covers a small region, it does make traveling in the area much more pleasant. For those of us who live in, or near, downtown Toronto flying out of the YTZ (a.k.a. Billy Bishop airport, a.k.a. Toronto City Centre, a.k.a. Toronto Island) saves the painful trip out to Pearson. More importantly, the overall experience is much nicer than most North American airlines. The staff, both ground and in-flight, are friendly and helpful. The planes are nice and new. The lounges, for us common people, are like business class. Hell they even give you food and booze on a short domestic flight. In brief, our weekend in Boston was already going well before we touched down.

Sleeping in Style Too

After landing and collecting our bags, it was a short cab ride to our hotel in downtown Boston, near the water in the downtown/financial district. I’m not going to lie, hotels in Boston aren’t cheap. We watched hotel discount sites for months in the lead up to the trip, hoping to find a steal and I’m sure if you work at it, you could find a way to shoestring it. In the end we managed to get a discounted rate at the Intercontinental, so we were livin’ the highlife for the weekend. The location was great as we could walk to the wharf and downtown in minutes.

Our first night in Boston was pretty low-key, dinner in a basement sports bar near Faneuil Hall in the Quincy Market area. Despite being in Boston, I elected to have the Buffalo wings. The wings were fine, nothing to blog about… oops…but my favourite part was the wetnap, or “moist towelette” to be brand agnostic. When I eat wings, scrubbing my messy fingers and face with the lemony freshness is part of the experience. I must just look like a messy eater because typically, my order of wings comes with an extra handful of wetnaps and a conspiratorial “just in case” from the waitress.

In this case the waiter gave me nothing. When, face covered in sauce, I did ask for one he disappeared for awhile before returning with a single packet, explaining that it was the last one. You know when you watch a mummy movie and they open the sarcophagus for the first time and there’s that desiccated puff of dust? Well, that’s what happened when I opened this packet. It was the least wet wetnap I have ever seen. Needless to say, it didn’t do much to clean me up. With a little help from the bathroom sink I was presentable enough, or at least as presentable as I get.

After dinner we stopped in at another of the many Irish pubs to take in some live music before deciding to call it a night and get some rest for what promised to be an eventful day of exploring.

Boston – You can fit more than you think into a day.

If you’re reading this, there’s a good chance that you know Katy. If that’s the case, it will come as no surprise when I say that Katy is organized. I mean, really organized. She is a planner and likes to know in advance what we will be doing. It’s not that she doesn’t appreciate unexpected detours, just that she hates to waste the limited time we have on our trips. I, on the other hand, am much more of a fly-by-the-seat-of-my-pants kind of person. The one exception being – and this has changed from when I was younger – I do like to have a place to sleep arranged. While you might think this could lead to conflict, it ends up making us complementary in a way that works: Katy plans and I roll with it. She wants me to plan more, but not really, because I might not do it right. Courtney and Greg, were also quite happy to let Katy take on the roll of tour leader for the trip.

Before the trip Katy had identified 11 key activities/sights for the weekend and even broken them out by day to make sure we had time to see it all.

Katy's Boston Action List

As the four of us set off Saturday morning we decided to start with a return to the Quincy Market area where we could pickup our Go Boston cards and grab some breakfast. Faneuil Hall is an old merchant building that was renovated in the 70s. While a bit touristy (we are tourists after all) it was a good place to pick up a quick bite to go, with lots of different food options, most of them on the “fast” side of things.

Faneuil Hall is also only a short walk to the wharf where, after talking to several of the many similar trolley companies, we finally figured out which one was ours. With the help of the trolley, we got a quick look at many of the Boston sights we didn’t plan on seeing in great detail: Fenway Park, MIT, Harvard, Chinatown. It was when we saw Cheers that we decided it was time to “hop-off”. I didn’t realize before we went to Boston that the outside of Cheers that you see on the tv show isn’t the same bar that they use for the inside. From the way the trolley driver talked about it, this is both shocking and appalling to many first time visitors. I can’t say any of our group was all that upset, we were only interested, mildly at that, in seeing the sign on the outside. Personally, I always thought the inside looked a lot like every other pub.

Katy and me in front of some bar with a line.

We were lucky, as the weather was pretty much perfect. So, after a couple of the requisite tourist pictures at Cheers we decided to continue on foot; always my favourite way to see a new place anyway. Boston is a very nice city with a lot of history. We had a great time walking along the Freedom Trail and through Boston Common. Eventually our semi-aimless wandering (though Katy kept us ticking off the list as we went) turned into a poorly targeted search for a patio. Employing the strategic approach of a Timbits hockey team, bumbling along without a real sense of direction, we ended up in Back Bay at a festival of some sort along the Esplanade before finding a patio that met our strict requirements: available seats and alcohol to be purchased.

As we settled into our table we realized that aside from the Aquarium (it was far too nice a day to be inside) and the whale tour, which we had booked for the following day, we had seen everything on Katy’s carefully prepared list. With this newfound free time we decided to really embrace some local culture. Sure, for some this would mean seeing more of Boston’s many sights, or digging a little deeper into the history, for us it meant an afternoon relaxing on a patio, like the locals.

Tough to beat Sangrias on a sunny patio.

As the afternoon wound down, our waiter asked if he could close out our bill as his shift was over and it was his turn to go for a drink. Greg, wisely spotting an opportunity to follow a local, asked where he was planning to go for his drink. “Actually,” he answered, “there’s a beer festival on. You guys should come.” Random beer festival in a new city on a beautiful sunny afternoon? Even better, it was within walking distance of our hotel. It didn’t take us long to accept.

As we walked towards the festival, thick clouds started to roll in over the city from the Atlantic. Combined with the fact that we would be there as night fell, we decided to stop by the hotel and grab some warmer clothes, a wise decision as it turned out.

Cloudy, Cloudy, Cloudy Beer

After the ladies spent some time convincing the security guards that they were in fact over 21 and that their Canadian drivers licenses were indeed real we headed into the tents. (Sadly, Greg and I did not have this problem and the clincher for their getting in was Courtney’s exasperatedly pointing at Greg and saying “I’m married to that guy!”)

Truth be told, we had all been to better beer festivals. The beer was all from one company (Harpoon), it was actually in the brewery’s parking lot, and the beer wasn’t very good. That said, the clouds continuing to pour in from the ocean made for an interesting, albeit cold, venue and we managed to enjoy ourselves. In fact, we had so much fun, and were so inspired by the clouds rolling in, we wrote a song, but that’s a story for another day.

You mean like a place where they tell you to f*&%-off?

After a while hunger kicked-in and we started working on a place for dinner. We decided the best way to find good local food was to ask a local. Again, Greg took the lead on this one. Spotting a fireman, oddly in dress uniform, Greg headed off to get a recommendation. After looking quite perturbed by Greg’s approach he quickly recommended a nearby favourite of his. It turns out we do not share restaurant tastes with this particular fireman. Then again we aren’t 20 year olds looking to pick-up, so I guess we should have known better.

After dinner we hopped into a cab to head back to the hotel for the night. Or so we thought. If you haven’t gathered this, Greg is a very sociable person with a knack for putting strangers at ease. He also loves chatting with cabbies. As we drove toward the hotel, Greg asked the cab driver what his favourite bar was, his local. In a thick Boston accent, his response was, “what, you mean like a place where they tell you to f*&%-off?” To which Greg responded, “um yeah, I guess, if that’s where you’d go”. Before anyone could say anything else, the cabbie quickly made a u-turn and we were on our way to South Boston, a working class Irish neighborhood.

When we got to the bar, the driver hopped out and immediately introduced us to two guys standing out front. Comfortable that we would be alright, he gave us a card with a number to call when we were ready to leave, hopped in his cab and took off. When we walked in, the bar was mostly empty with only a small group, all of whom watched us enter in silence. I’m pretty sure the music didn’t stop with a screech… it just felt that way.

We took a table near the front and I headed to the bar to get drinks. On the bar was a giant neon green vat of liquid. When I asked what it was, I was told that it was free and “only for the ladies”. A second try at what was met only with a reminder that it was “only for the ladies”. So, the ladies each got a mystery drink.

In case you're wondering, they're for the ladies.

We weren’t there long but I guess we were deemed acceptable by the locals. Before long they were back to taking turns picking songs on the jukebox, many of which had a certain Irish revolutionary feel to them. For our part we were singing along with them where we could and generally had a great time. I can’t for the life of me remember what the bar was called or how you get there, but if you’re looking for somewhere to go in Boston for a drink, it might just be worth asking a cab driver.

It had been a great but busy day, so when we got in the cab the second time, we managed to make it all the way back to the hotel. Besides, we had our big whale tour to rest up for…

Wow, thanks for making it to the bottom. Come back for the whale tour, I promise it’s worth it.

You made the small trip sound pretty interesting…looking forward to visiting with Katy leading the way!! I wonder if she’ll take me on the trail to the green drink for ladies??? I’m counting on it Katy…you don’t want to disappoint your mom! 🙂 I look forward to reading about your Whale Tour…best story ever!! 🙂